Synthesis of pyranicin and its inhibitory action with bovine heart mitochondrial complex I

Yasunao Hattori; Shin-ichi Furuhata; Motonori Okajima; Hiroyuki Konno; Masato Abe; Hideto Miyoshi; Tetsuhisa Goto; Hidefumi Makabe

doi:10.1021/ol702902w

Synthesis of pyranicin and its inhibitory action with bovine heart mitochondrial complex I

Org Lett. 2008 Mar 6;10(5):717-20. doi: 10.1021/ol702902w. Epub 2008 Feb 6.

Authors

Yasunao Hattori¹, Shin-ichi Furuhata, Motonori Okajima, Hiroyuki Konno, Masato Abe, Hideto Miyoshi, Tetsuhisa Goto, Hidefumi Makabe

Affiliation

¹ Interdisciplinary Graduate School of Science and Technology, Shinshu University, 8304 Minaniminowa Kami-ina, Nagano 399-4598, Japan.

PMID: 18251547
DOI: 10.1021/ol702902w

Abstract

Total synthesis of pyranicin was achieved using Cl2Pd(CH3CN)2-catalyzed diastereoselective cyclization of the allylic ester as the key step. The inhibitory activity of this compound for mitochondrial NADH-ubiquinone oxidoreductase (complex I) was slightly poorer than that of ordinary mono-THF acetogenins such as cis-solamin.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetogenins / pharmacology
Animals
Annonaceae / chemistry
Cattle
Electron Transport Complex I / metabolism*
Fatty Alcohols
Furans / chemistry*
Furans / metabolism
Lactones / chemistry*
Mitochondria, Heart / drug effects*
Molecular Structure

Substances

Acetogenins
Fatty Alcohols
Furans
Lactones
cis-solamin
pyranicin
Electron Transport Complex I